A Pd confined hierarchically conjugated covalent organic polymer for hydrogenation of nitroaromatics: Catalysis, kinetics, thermodynamics and mechanism

Article abstract of DOI:10.1039/d0gc01469a

Herein, we propose a fast and scalable synthesis of a triazine based hierarchically conjugated covalent organic polymer under solvent and additive free conditions through a single step process. The synthesized material CCTP (Cyanuric Chloride-Thiourea-Polymer) was thoroughly characterized by various physicochemical techniques. The CCTP exhibited regular sponginess and excellent chemical as well as thermal stability. The solvent and additive free approach for CCTP synthesis provides a sustainable alternative for classical solvothermal methods. The CCTP was immobilized with Pd (0) and subsequently a heterogeneous material Pd&at;CCTP was obtained, which was used as an efficient catalyst for the hydrogenation of nitroarenes. The rate constant and Ea were measured to be 2.08 × 10-2 s-1 and 15.67 kJ mol-1 respectively and thereafter other thermodynamic parameters like ΔH, ΔS and ΔG for the hydrogenation of p-nitrophenol were also calculated. The obtained results indicate that the catalytic hydrogenation of p-nitrophenol is a non-spontaneous and endothermic process. We have also investigated the effect of surfactants (NH4OH, FA, and N2) on the reaction performance, and consequently NH4OH and FA both slow down the reaction while N2 doesn't affect the reaction medium. Further, we calculated the rate constant for the hydrogenation of 2,4-dinitrophenol and 2,4,6-trinitrophenol. An array of nitroarenes were further reduced to extend the substrate scope at RT; high TOFs were observed. Besides, Pd&at;CCTP showed excellent reusability in hydrogenation reactions without evident performance falloff.

Full text of DOI:10.1039/d0gc01469a

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Paul T. Anastas et al.
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Green Chemistry
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DOI: 10.1039/D0GC01469A
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DOI: 10.1039/D0GC01469A

&'()*( +, -,. )+/0*. 1)234-*
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DOI: 10.1039/D0GC01469A
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&'()*( +, -,. )+/0*. 1)234-*
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DOI: 10.1039/D0GC01469A
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R-4.2,>8(-,'= R)14-,>8(-,' )-+ R-4.2,>8(-,' 4,-* Q)O.(2
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&'()*( +, -,. )+/0*. 1)234-*

Page 5 of 10
Green Chemistry
View Article Online
DOI: 10.1039/D0GC01469A

&'()*( +, -,. )+/0*. 1)234-*
Green Chemistry
Page 6 of 10
View Article Online
DOI: 10.1039/D0GC01469A
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&'()*( +, -,. )+/0*. 1)234-*

&'()*( +, -,. )+/0*. 1)234-*
Green Chemistry
Page 7 of 10
View Article Online
DOI: 10.1039/D0GC01469A
D#.)$*+ M*3'
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2()5.4,- 14<.02( K)* O4'.(2(+ .82,038 1452,RN058-(2 O0--(' 4-
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K).(2 )-+ (<.2)5.(+ K4.8 (.8:' )5(.).(C !8( (<.2)5.(+ (.8:'
)5(.).( K)* +24(+ ,6(2 )-8:+2,0* W);I@X )-+ 5,-5(-.2).(+
0-+(2 :.0+#C !8( >2,+05. K)* >024O4(+ N: 5,'01-
582,1).,32)>8: Q4O 2(T042(+SC
2()5.4,- K)* >)**(+ .82,038 K).(2C @-5( .8( M#' O01(* *.,>
5,14-3 ,0.= .8( 2()5.4,- 14<.02( K)* 5,,'(+ +,K- ., 2,,1
.(1>(2).02(= ) >)'(R:('',K 5,',2(+ *,'4+ K)* ,N.)4-(+C ". K)*
K)*8(+ K4.8 K).(2= h(@M )-+ !MYC A O4-)' K)*84-3 ,O 1).(24)'
K)* +,-( K4.8 )5(.,-(= +24(+ 0-+(2 6)5001 )-+ -)1(+ )*
##!&C ". K)* K('' 58)2)5.(24P(+ 0*4-3 6)24,0* >8:*4,58(145)'
.(58-4T0(* '4G( Y!" = BD#R#&hAI= k&I (.5C
G,$0('4&4 #% !Z66K A 14<.02( ,O )* *:-.8(*4*(+ ##!& Q;^7
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4-52(1(-. ,O )TC W)]MX +2,> K4*(C !8( 14<.02( .02-(+ ., 32(:
411(+4).(': )O.(2 )++4.4,- ,O )TC W)]MXC ". K)* O02.8(2 *.422(+
O,2 X7 14-= 2(*0'.(+ ) N2,K- 5,',02(+ *,'4+ Q&+U##!&S K)*
O4'.(2(+ )-+ K)*8(+ *(6(2)' .41(* K4.8 K).(2 )-+ )5(.,-(C
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6#$"+.4&#$4
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*0*.)4-)N'( *:-.8(*4* ,O ) -(K #,6)'(-. @23)-45 &,':1(2 Q#@&S
0*4-3 4-(<>(-*46( >2(502*,2* .84,02() )-+ 5:)-0245 58',24+(C
!8( -(K': *:-.8(*4*(+ #@& Q##!&S K)* 0*(+ O,2 (OO454(-.
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1).(24)' &+U##!&C !8( *0*.)4-)N4'4.: ,O 5).)':*. 5,1(* O2,1
*,'6(-. )-+ )++4.46( O2(( *:-.8(*4* 1(.8,+= K8458 346(* )
32((-(2 )'.(2-).46( ,O *,'6,.8(21)' 1(.8,+,',3:C V( 8)6(
5)224(+ ,0. G4-(.45 )-+ .8(21,+:-)145 4-6(*.43).4,- ,O
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)-)':*(+ .8( (OO(5.* ,O *02O)5.)-.*C I0N*(T0(-.': .8( )*R
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,>.414P(+ (OO454(-54(*C !8( 2).( 5,-*.)-. )-+ %) ,O &+U##!& O,2
8:+2,3(-).4,- ,O XRW& K(2( ,N.)4-(+ ., N( ;C7`LB7R; *(5RB )-+
B^C[_ G91,'RBC A++4.4,-)'':= &+U##!& *8,K(+ (<5(''(-.
5).)':.45 )5.464.: O,2 ;=XR?W& )-+ ;=X=[R!W& )-+ )'*, (<84N4.(+
>(2O,21)-5( ,O &+U##!& K)* (6)'0).(+ N: 8:+2,3(-).4,- ,O
*0N*.4.0.(+ -4.2,)2(-(* 0*4-3 (<5(** ,O W)]MX QmB77 (T046)'(-.* .,
-4.2,)2(-(SC "- ) .:>45)' >2,5(+02(= ; 1$ ,O )- )T0(,0* +4*>(2*4,- ,O
&+U##!& QB 13F1$S K)* )++(+ ., .8( 14<.02( ,O ; 1$ ,O XRW& Q7C7^
hS )-+ W)]MX QB77 (TCS 0-+(2 5,-.4-0,0* *.4224-3 ). !C W(<.= ) B7
s$ ,O .8( 2()5.4,- 14<.02( K)* K4.8+2)K- )O.(2 (6(2: ;7 *(5,-+* )-+
+4'0.(+ K4.8 ; 1$ ,O K).(2C !8( +4'0.(+ *,'0.4,- K)* T045G': O4'.(2(+
0*4-3 *:24-3( O4'.(2 )-+ )-)':*(+ 0*4-3 bqR64* *>(5.2,1(.(2C !8(
(<>(241(-. K)* )'*, >(2O,21(+ K4.8,0. 5).)':*. )-+ K4.8,0. W)]MX
0-+(2 *)1( 2()5.4,- 5,-+4.4,-*C #,-.2,''(+ (<>(241(-.* K(2(
>(2O,21(+ N: 6)2:4-3 .(1>(2).02( ! ., X7 )-+ .8(- ^7 ,#C !8( *)1(
>2,5(+02( K)* 2(>().(+ O,2 8:+2,3(-).4,- ,O ;=XR?W& )-+ ;=X=[R (<5(''(-. 2(0*)N4'4.:C !8( *055(**O0' )>>'45).4,- ,O
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>,':1(2*C
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11,'S= &+U##!& Q7CE_ 1,'o &+= B7 13S )-+ W)]MX Q7CD_` 3S K(2(
.)G(- 4- B7 1$ ,O M;@ )-+ *.422(+ ). !C !8( 2()5.4,- >2,32(** K)*
1,-4.,2(+ 0*4-3 !$# )-+ )O.(2 5,1>'(.4,-= 5).)':*. K)* *(>)2).(+C
!8( O4'.2).( K)* (<.2)5.(+ K4.8 (.8:' )5(.).( )-+ +24(+ 0-+(2 6)50,C
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bqRq4* )N*,2>.4,- *>(5.2,*5,>: )-+ .8(42 2(*>(5.46( 4*,').(+
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6)5001C I0N*(T0(-.':= -(<. 8:+2,3(-).4,- 2()5.4,- K)*
>2,32(**(+ K4.8 2(5,6(2(+ &+U##!& 5).)':*. )-+ .8(
>2,5(+02( K)* 2(>().(+C !, 4-*>(5. .8( 5).)':.45 *.)N4'4.:=
1,2>8,',3: )-+ 1(.)' '()584-3 )O.(2 -4-( 5).)':.45 20-*= .8(
2(5,6(2(+ 5).)':*. K)* 58)2)5.(24P(+ )-,.8(2 .41( N: Y!R" =
%?k= &k ? )-+ Y%I%hC !8( 2(*0'.* ,N.)4-(+ K(2( *43-4O45)-.':
*.()+: K4.8 &+U##!& )* +4*50**(+ N(',KC
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b-46(2*4.: ,O ?('84 O,2 >2,64+4-3 .8( -(5(**)2: 4-O2)*.205.02(
)-+ bI"#= b-46(2*4.: ,O ?('84 O,2 58)2)5.(24P).4,- )-+ ,.8(2
2(T042(+ O)54'4.4(* 64PC " )-+ Wh 2(*0'.*C ?H 32).(O0'':
)5G-,K'(+3(* #I" = W(K ?('84= O,2 >2,64+4-3 I YC IJA
)5G-,K'(+3(* O4-)-54)' *0>>,2. O2,1 I% ]= W(K ?('84
QI% ]FYFEE_X!;7RB_S )-+ b-46(2*4.: ,O ?('84= "-+4)C
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M#0'4 *$! )'%')'$"'4
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&'()*( +, -,. )+/0*. 1)234-*

&'()*( +, -,. )+/0*. 1)234-*
Green Chemistry
Page 8 of 10
View Article Online
DOI: 10.1039/D0GC01469A
AJKI6L9
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^C
YC M,OO1)--= hC #,2-('40*= 9C h,2('' )-+ hC Y2}N)= A'*%QA DDC
"-%/A ?',A I(A= ;77[= X^= D;B[RD;^BC
&C &0.84)2)/= ICRhC #8,= HCR C $(( )-+ VCRIC A8-= OA R.,%$A DXC
"-%/A A= ;7B^= D= [_E;R[_E_C
HC #04= 9C ?0= HC $40= HC H0= IC V)-3= MC &)-3= |C $4)-3 )-+ 9C D^C
H0= L#13/A "-%/A= ;7B`= E= ;[XDR;[XEC
|C $4 )-+ HCRVC H)-3= OA R.,%$A "-%/A 2= ;7B_= ^= E;_`RE;E7C D[C
qC I)+8)*46)1= C ])')*)2)6)-)-= #C #84.842)4G01)2 )-+ AC
9C !8,2-.,-= hC h5#)'':= &C @224* )-+ 9C V(4-N(23= L+51)0
U%.1,- S% A= BEE[= BBB= ;E`C
nC Y42+)0* )-+ AC A81)+= ?',A OA I':)$#'A S%&A= ;7B7= X= _E^R
`7[C
CR$C V)-3= ?CR&C $4= $CR9C V)-3= kC |8)-3= |CRHC |8,0= 9CR$C
h0 )-+ |CRhC I0= 7.1,#' @$.'&A= ;7BE= X`= B7^BRB7^EC
&C &C n84142(= $C |8)-3= bC AC J4-3)= ~C n0,= ]C 94)-3 )-+ hC
9)2,-4(5= OA R.,%$A "-%/A A= ;7BE= _= E[B`RE[;`C
C AN)P)24= AC C h)8/,0N )-+ 9C I8)24).4= OA U.V.$(A R.,%$A=
;7BE= D[[= XDERX^BC
?C #8(-= kC |80= 9C M0)-3= nC V)-3= HC |8),= YC #8(-= 9C V(4=
|C I,-3 )-+ HC |8),= A'.1A "-%/A= ;7B`= E7= E7X`RE7^XC
ICRIC |8)-3= WC H)-3= kC |80)-3= $C (-= qC W).)2)/)-= |C #04=
MC I4= kC k4-= ICR~C W4 )-+ 9C |8)-= N0)A S% A= ;7BE= E= BREC
hC ?ZA'(**)-+2,= qC %*>,*4.,= %C hC &,2>,2).,= ?C ](2.,= hC
(-P4= IC n4)5,NN(= nC I5,..4= &C #,-*,'4= nC q)')*.2, )-+ YC
A-+)',2,= I':)$#'A L#11+,A= ;7B`= ;X;= B^X[RB^^[C
MC M)2.4G)4-(-= OA @$.0% I1%/A R%(A 2)#1A= ;77^= B`= D7ERDB`C
&C ])')*0N2)1)-4)-= !C ])')10203)-= ICRhC #8(- )-+ !CRVC
#8(-= OA U.V.$(A R.,%$A= ;7BE= D[B= B;DRBDDC
AC %':= hC ])0+0= 9CR&C ])*': )-+ hC @C IC AC @C J)-G,0= OA
U.V.$(A R.,%$A= ;77E= B_B= X7^RX7EC
[C
_C
I46)= "-%/".,"-%/= ;7B`= B7= D`DDRD`XXC
hC 9C ],/+:*= 9C 9(2,1(-,G= AC !8,1)* )-+ hC A-.,-4(..4=
A(:A R.,%$A= ;7B7= ;;= ;;7;R;;7^C
IC M03= $C I.(3N)0(2= MC @8= hC M42*58(2 )-+ ]C qC $,.*58=
"-%/A R.,%$A= ;7B^= ;_= `77BR`7B7C
D_C
D`C
DEC
`C
EC
B7C
AC (-3)2)/= &C &0.84)2)/= HC M)'+,2)4= WC IC M(,= ICRJC
MK)-3= HCRJC M)-= IC JK,-= VCRIC A8- )-+ HC IC M08= A"N X7C
A 1A R.,%$A ?',%$8.0%&= ;7B[= `= `EX_R`E^^C
$C !)- )-+ ]C !)-= "-%/A N#0A S%:A= ;7B_= X[= DD;;RDD^[C
!C n(-3= IC H(= |C |80 )-+ VC |8)-3= OA R.,%$A "-%/A A= XBC
BBC
B;C
;7B`= [= ;`7`R;`B[C
AC JC h)-+)'= 9C h)81,,+ )-+ 9C ]C ])(G= "-%/P.'#R.,=
;7B_= D= D_DRDEBC
hC nC n,(*.(- )-+ hC A1*'(2= A"N R.,%$).1& 4%,,A= ;7BE= B=
D7RD[C
X;C
XDC
XXC
BDC
BXC
B^C
IC ]C M)+(2'(4- )-+ C &C I58K)2P(-N)58= I':)$#'A N0)A
@%0-'#1A= BEED= ;_= DB[RD;[C
IC WC J8)..)N= IC %C AC W)41= hC %'RI):(+= AC AC %' ])2+)-= AC
@C %'P,38N:= AC AC ](G84. )-+ AC %'RY)8)1= P%Q OA "-%/A= X^C
;7B[= X7= E^[^RE^_`C
I0N,+8= JC &2)G)*8 )-+ ?C !C h)*2)1= 7.1,#' @$.'&A= ;7;7=
"C "N2)841= #C A.8)-)*(G,0= nC h)-,'4*= AC J)'.P,3',0= WC JC
W)*4G)*= YC J).*)2,*= %C ?(6'4-= AC nC J,-.,* )-+ &C Y)')2)*=
OA U.V.$(A R.,%$A= ;7BE= D_;= D_RXXC
B[C
B_C
XE= B77_RB7B7C
&C ]8)-/)= IC JC ?)*= JC ]80-4)= ?C &2)+8)-= !C M):)*84= HC
M4/4G).)= IC "2'( )-+ AC ]8)014G= A"N N+&,.)'.51% "-%/A X_C
I'*A= ;7B_= [= ;7;R;7EC
X[C
%C n,5'4G= %C #82P(*54/)-*G)= %C J0*14(2(G )-+ 9C :-G,K*G4=
L#$,A I1%0,$#0-)/A A0,.= ;7BE= D_= DX^RD^_C
HC hC &,2,-4G= JC qC q:32)-(-G,= ?C n2:G, )-+ ?C !C n2:G,=
"-%/A N#0A S%:A= ;7BE= X`= ^;X;R^;[^C
B`C
BEC
;7C
;BC
;;C
;DC
;XC
IC h0G8(2/((= hC ?)*= AC h)--)= C J24*8-) )-+ IC ?)*= X`C
"-%/A R.,%$A= ;7BE= DB= DE;ERDEX7C
$C k0= YC V)-3= kC n(= C $40= hC k0 )-+ 9C H)-3= R)0$# #$#+& XEC
R%&# #$#+& R.,%$A= ;7BE= ;`_= [^R_7C
I0N,+8= JC &2)G)*8= JC #8)0+8)2: )-+ ?C !C h)*2)1= A 1A ^7C
".,.1A A;T%'A= ;7;7= ^ED= BB_XBBC
MC $6= kC |8),= MC W40= IC M(= |C !)-3= YC V0 )-+ 9C &C n4(*:= ^BC
OA U.V.$(A R.,%$A= ;7BE= D[E= XEXR^7;C
MCRHC V0= ?C I)4G4)= #CR&C $4-= YCRIC V0= nC !C Y(: )-+ MCRhC ^;C
J),= L#13/%$= ;7B7= ^B= XD^BRXD[BC
hC #8)0+8)2:= $C I4-38= &C (G8)= qC #C I246)*.)6) )-+ &C ^DC
h,8)-.:= "-%/A I'*A OA= ;7BE= D_`= B;;;D[C
JC ?(:= hC &)'= JC #C ,0.= IC J0-/)..0 M= AC ?)*= C ^XC
h0G8(2/((= bC JC J8)20' )-+ C ])-(2/((= OA A/A "-%/A N#0A=
MCRTC V)-3= 9CR>C H)-= |CR1C |8)-3 )-+ VCROC #8)-3= S%.0,A
M)'%,A ".,.1A 4%,,A= ;77E= E_= EBREEC
AC A-*)24= C AC ])+8( )-+ IC IC n)2/(= A"N X/%*.= ;7BE= X=
BXED_RBXEX[C
|C k4,-3= MC |8)-3= VC |8)-3= ]C $)4 )-+ nC H),= "-%/A I'*A
OA= ;7BE= D^E= BDRDBC
I0N,+8= WC JC h,38)= JC #8)0+8)2:= nC J01)2 )-+ ?C !C
h)*2)1= A"N X/%*.= ;7B`= D= B[D__RB[D`^C
!C &)2)-+8)1)-= hC ?C ?(: )-+ IC JC ?)*= T$%%' "-%/A=
;7BE= ;B= ^X[ER^^77C
I0N,+8= JC #8)0+8)2:= JC &2)G)*8 )-+ ?C !C h)*2)1= A 1A
N+$8A N0)A= ;7;7= ^7E= BXXE7;C
&C &0.84)2)/= HCR C $((= IC |8)-3 )-+ VCRIC A8-= OA R.,%$A
"-%/A A= ;7B[= X= B[;``RB[DBBC
;7B_= BDE= BD7`DRBD7EBC
^^C
^[C
^_C
^`C
^EC
9C hC W,.(*.(4- )-+ AC J).P= "-%/YI+$A OA= ;77[= B;= DE^XR
DE[^C
&C &0.84)2)/ )-+ JC &4.5801)-4= T$%%' "-%/A= ;7BX= B[=
X;;DRX;DDC
?C H)+)6 )-+ IC JC AK)*.84= 7.1,#' @$.'&A= ;7;7= XE= B_ER
B`[C
HCR#C $0= 9C #8(-= ACR9C V)-3= WC ]),= 9CR9C Y(-3= VC V)-3
)-+ $C I8),= OA R.,%$A "-%/A "= ;7B^= D= _DR_`C
]C #C &).2)= IC JC ?)*= AC n8,*8= &C h,4.2)= hC A++45,).= IC
h4.2)= AC ]8)014G= IC ]8)..)58)2:) )-+ AC &2)+8)-= OA
R.,%$A "-%/A A= ;7B`= [= B[[^^RB[[[DC
;^C
;[C
;_C
;`C
;EC
D7C
~C I0-= ]C A304')= 9C &(21)-= WC W30:(- )-+ IC h)= OA A/A
"-%/A N#0A= ;7B[= BD`= B^_E7RB^_E[C
?C H)+)6 )-+ IC JC AK)*.84= P%Q OA "-%/A= ;7;7= XX= BD;7R
BD;^C
HC k0= IC 94-= MC k0= AC W)3)4 )-+ ?C 94)-3= "-%/A N#0A S%:A=
;7BD= X;= `7B;R`7DBC
&C |8)-3 )-+ IC ?)4= OA R.,%$A "-%/A A= ;7B_= ^= B[BB`R
B[B;_C
&C $C #8(0-3= IC JC $(( )-+ #C &C J0N4)G= "-%/A R.,%$A= ;7BE=
DB= BE7`RBEBEC
JC &2((.= nC n0>.)= hC J,.)'= IC JC J)-*)'= ?C ]C I)'0-G(= MC [7C
JC I8)21)= IC #8)-+2) I)8,,= &C q)- ?(2 q,,2. )-+ IC ,:=
"$3&,A T$#Q,- 7%&A= ;7BE= BE= ;^;^R;^D7C
HC $4= JCRMC V0= WC M0)-3= IC ?)')>).4= ]CR9C I0= $CRHC 9)-3= "C
C n(-.'(= ?C 94)-3 )-+ ?CRVC V)-3= I'%$*3 N,#$.*% R.,%$A=
;7B`= B;= D7RD[C
DBC
C V)058,>(= OA I':)$#'A W+.1A= BE_`= _= X^ERX_;C
= e OA P./%C= ;7B;= <<= BRD
!84* /,02-)' 4* f !8( ,:)' I,54(.: ,O #8(14*.2: ;7<<
&'()*( +, -,. )+/0*. 1)234-*

&'()*( +, -,. )+/0*. 1)234-*
Green Chemistry
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DOI: 10.1039/D0GC01469A
D#.)$*+ M*3'
AJKI6L9
[BC
HC $,-3= JC $4)-3= 9C W40= kC !,-3= ]C H0)- )-+ 9C h)= P%Q OA
"-%/A= ;7B^= DE= ;E``R;EE[C
[;C
[DC
!C ?4..2458= L-3&A N,.,+& N#1)()= ;777= B`;= XX_RX^^C
HC k4(= ]C $40= HC $4= |C #8(-= HC #), )-+ ?C 94)= P%Q OA "-%/A=
;7BE= XD= B;BB`RB;B;^C
[XC
[^C
[[C
[_C
[`C
[EC
_7C
_BC
HC ?0)-= kC k0 )-+ $C |8,0= S%.0,A Z+'0,A L#13/A= ;7BE= BX;=
^DR^EC
JC I)21)8= 9C &)'= !C JC h)/4 )-+ IC &2).48)2= A"N N+&,.)'.51%
"-%/A I'*A= ;7B_= ^= BB^7XRBB^B^C
YC $40= kC $40= ?C A*.205 )-+ MC n0= OA "#11#)( ?',%$8.0% N0)A=
;7BE= ^DD= B[BRB_7C
VC n,-3= ~C V0= nC 94)-3 )-+ nC $4= OA R.,%$A "-%/A A= ;7BE=
_= BDXXERBDX^XC
IC C !8)K)2G)2= ]C !8,1N)2(= ]C IC h0-+( )-+ WC ?C
J80>*(= SN" A(:A= ;7B`= `= D`D`XRD`DE7C
kC I8)-= WC I04= VC $40= hC $40 )-+ 9C $40= OA R.,%$A "-%/A A=
;7BE= _= XXX[RXX^7C
|CRIC $6= kCRHC |80= MCR]C h(-3= 9CR9C Y(-3 )-+ ACR9C V)-3= OA
"#11#)( ?',%$8.0% N0)A= ;7BE= ^D`= DXERD^[C
HC #8(-= !C V0= nC k4-3= HC J,0= ]C $4= kC V)-3= hC n),= $C
#8(-= HC V)-3 )-+ 9C H)-3= ?'(A I'*A "-%/A S%&A= ;7BE= ^`=
B^B^BRB^B[BC
_;C
_DC
HC V)-3= ~C $4= &C |8)-3= ?C @Ä#,--,2= C IC q)21)= hC H0
)-+ ?C M,0= OA "#11#)( ?',%$8.0% N0)A= ;7BE= ^DE= B[BRB[_C
HC |8),= ]C #),= |C $4- )-+ kC I0= I':)$#'A #11+,A= ;7BE= ;^X=
BB;E[BC
!84* /,02-)' 4* f !8( ,:)' I,54(.: ,O #8(14*.2: ;7<<
OA P./%C= ;7BD= <<= BRD e ]
&'()*( +, -,. )+/0*. 1)234-*

Green Chemistry
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DOI: 10.1039/D0GC01469A